Holiday Rentals in Oakland

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Oakland

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
10.0 out of 10, Exceptional, (32)
"This was a very clean and perfect place for a girls' or family trip! Everything we needed was there. It was so comfy!! Beth was very easy to get in touch with. Will stay again!!"
Cozy 3 bedroom home! Located in the heart of Arthur, Illinois
Brickway Retreat
9.6 out of 10, Exceptional, (19)
"Easy process, very clean and great location. "
The price is €166
includes taxes & fees
23 Nov - 24 Nov
Brickway Retreat
A Luxury Family Mill Creek Lake Retreat
10.0 out of 10, Exceptional, (65)
"We had a fantastic time at A Luxury Family Mill Creek Lake Retreat. There isn't a single thing I can really complain about. The property is stunning, well stocked and maintained, and straightforward to get to. Ample seating for dining, playing board games, and relaxing by the fire. We'd gladly stay again with our extended family."
A Luxury Family Mill Creek Lake Retreat
Newly updated and cozy home! Located near downtown!
9.2 out of 10, Wonderful, (7)
"I stayed at this property for 2 days due to work and I was highly satisfied. The house was very welcoming, smelled amazing, and was decorating nice.The host was exceptional and made sure all of my needs were met. The fact that the essentials were provided plus some made my stay even better. I didnt have to worry about packing everything under the sun because it was already there. I would definitely recommend to anyone looking to visit Mattoon. "
The price is €167
includes taxes & fees
30 Nov - 1 Dec
Newly updated and cozy home! Located near downtown!
Country Home Near EIU & Lake Charleston!
9.6 out of 10, Exceptional, (9)
"This is a very nice place to stay. It has everything you need. Very clean and comfortable. "
Country Home Near EIU & Lake Charleston!
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
10.0 out of 10, Exceptional, (12)
"Great stay!"
Great home to unwind 15 minutes from Champaign Urbana and University of Illinois
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
9.8 out of 10, Exceptional, (20)
"Nice place. Good value for the money. The upstairs/downstairs is nice to have two levels. Didn’t see the lake. Very quiet neighborhood. Probably needs handrails for outside entrance and down to lower level in the house. Kitchen has about everything you would need. Would stay there again. "
FAMILY FRIENDLY LAKE HOUSE WITH FABULOUS SCREENED PORCH
Updated spacious 2 br Flat
9.0 out of 10, Wonderful, (2)
"Was great location for my stay. House had everything I needed. Great communication w the host. Highly recommend"
Updated spacious 2 br Flat
A frame getaway on the Embarrass River in Charleston, Illinois
2.0 star property
10.0 out of 10, Exceptional, (2)
"This little cabin by the river was such a nice place to unwind and explore all that the Willenborg Woods have to offer. The trails are clearly marked and take you through a variety of views. The hosts were responsive and helpful during the entire stay, with the highlight being a morning basket of farm fresh eggs, hot coffee, and a warm, delicious pastry. We could not recommend this rental enough!"
A frame getaway on the Embarrass River in Charleston, Illinois
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!
2.0 star property
Cozy RV on 149 acres in Charleston with AC, WiFi, and eight miles of trails!
Historic Charleston Home < 1 Mi to University!
6.0 out of 10, (2)
"Was in town for a couple days and this home was perfect for what we needed and is close to the square which was a great added bonus. Would definitely stay again."
Historic Charleston Home < 1 Mi to University!
Beautifully Restored Farmhouse in Marshall!
9.8 out of 10, Exceptional, (6)
"Great house, great space. Will be safer when smoke alarms and CO doctors are installed. Quiet setting. Nice kitchen."
Beautifully Restored Farmhouse in Marshall!
Historic Charleston Home < 1 Mi to University!
3.0 star property
Historic Charleston Home < 1 Mi to University!
Country Home Near EIU & Lake Charleston!
3.0 star property
Country Home Near EIU & Lake Charleston!
Charming House on EIU Campus, Near Sarah Bush Hospital
2.0 star property
Charming House on EIU Campus, Near Sarah Bush Hospital
Beautifully Restored Farmhouse in Marshall!
3.0 star property
Beautifully Restored Farmhouse in Marshall!
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions
Spacious 3Bed/3Bath Apt: Pet-Friendly, Gym, Minutes from EIU & Local Attractions
Cottage lake house nestled east of Mill Creek Park in Marshall IL
Cottage lake house nestled east of Mill Creek Park in Marshall IL
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Oakland
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Oakland you may be interested in

Comfort Suites Mattoon
2.5 star property
8.8 out of 10, Excellent, (651)
"We enjoyed our overnight stay at Comfort Suites Mattoon, IL. The staff members were very courteous and friendly, the hotel was extremely clean, check-in was quick and easy, breakfast was included, our room was quiet and the bed was comfortable. I only rated it 4 stars because the elevator was not working, however that did not affect us, as our room was on the first floor. The area that the hotel is located in is clean and there are plenty of shopping and dining options nearby. I would highly...
The price is €94
includes taxes & fees
23 Dec - 24 Dec
Comfort Suites Mattoon
Suite Dreams Hotel
2.5 star property
7.2 out of 10, Good, (397)
"I realize this is an older hotel, but some maintenance in some of the rooms would be nice. Repair torn carpet."
The price is €92
includes taxes & fees
23 Nov - 24 Nov
Suite Dreams Hotel
Unique Suites Hotel
2.5 star property
8.6 out of 10, Excellent, (601)
"Thank you. Great place to stay close to the university "
The price is €100
includes taxes & fees
23 Nov - 24 Nov
Unique Suites Hotel
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakland has to offer?

Cozy 3 bedroom home! Located in the heart of Arthur, Illinois : This holiday home rental outside of Oakland is located in the city centre, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

What can I see and do in Oakland?

While you're exploring the area, Walnut Point State Park and Fox Ridge State Park are a couple of picturesque spots to get outside and enjoy nature. Eastern Illinois University and Hippie Memorial are a couple of places you'll find in the wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.